Potassium Carbonate → N-(2-tert-butoxybenzyl)-3-(4-phenylpiperidin-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amine

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Reaction Steps

4-phenyl piperidin (0.21 g, 1.2 mmol), compound 19 (0.3 g, 0.86 mmol), KI (0.43 g, 2.59 mmol) and K2CO3 (0.59 g, 4.3 mmol) were added to 50 mL CH3CN, and the solution was refluxed under argon atmosphere for 12 h. After cooling to room temperature, the inorganic salts were filtered, and the filtrate was evaporated to dryness. The residue was redissolved in CH2Cl2 and chromatographed on a silica gel TLC plate that was developed with the following eluents: 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as yellow oil (36% yield). 1H NMR (CDCl3) δ 8.492 (dd, 1H, Ar), 7.619 (ddd, 1H, Ar), 7.571 (t, 2H, Ar), 7.272 (t, 2H, Ar), 7.203 (d, 2H, Ar), 7.167 (t, 1H, Ar), 7.107 (m, 2H, Ar), 7.024 (t, 2H, Ar), 3.770 (s, 2H, —CH2—), 3.695, (s, 2H, —CH2—), 3.003 (d, 2H, —CH2—), 2.524 (t, 2H, —CH2—), 2.459 (m, 1H, —CH—), 2.367 (t, 2H, —CH2—), 2.01 (ddd, 2H, —CH2—), 1.783 (m, 6H), 1.359 (s, 9H, —C(CH3)3). Mass Spec.=472.34 (M+H)+.

Provenance & Evidence